World Journal of Pharmaceutical Research
Vyas et al.
World Journal of Pharmaceutical
SJIFResearch
Impact Factor 5.990
Volume 4, Issue 10, 2877-2882.
Research Article
ISSN 2277– 7105
SYNTHESIS AND CHARACTERIZATIONS OF SOME NOVEL SCHIFF
BASE DERIVED FROM DIBENZALACETONE
K. M. Daraji, P. P. Darji, P. A. Patel, K. P. Damor, Z. M. Gadhawala, K. V. Goswami,
S. P. Vyas*
Organic Chemistry Research Lab., Chemistry Division The H. N. S. B. Ltd. Science College,
Himatnagar-383 001
ABSTRACT
Article Received on
17 Aug 2015,
Dibenzalacetone reacts with Various aromatic Amine, .Finally the
product were characterized by conventional and instrument methods.
Revised on 08 Sep 2015,
Accepted on 29 Sep 2015
KEYWORDS: Novel Schiff base, Dibenzal acetone, Amine.
*Correspondence for
Author
INTRODUCTION
S. P. Vyas
Azomethines are generally known as Schiff bases to honour Hugo
Organic Chemistry
Schiff, who synthesized such compounds. These are the compounds
Research Lab., Chemistry
containing characteristic -C=N- group. Several methods have been
Division The H. N. S. B.
reported for the preparation of azomethines. Selvam et.al
Ltd. Science College,
[1]
have
prepared sulfonamide and its derivatives as anti-HIV agents. More et.
Himatnagar-383 001
al [2] have marked the biological activity of Schiff bases synthesized
from aminothiazoles. Ernst Bayer
[3]
has reported some metallocomplex Schiff bases derived
from o-amino phenol. Schiff bases can be synthesized from an aromatic amine and a carbonyl
compound by nucleophilic addition forming a hemiaminal, followed by a dehydration to
generate an imine
[4]
. They are well known intermediates for the preparation of azetidinones,
thiazolidinones, oxadiazolines and many other derivatives. Azomethines exhibit a wide range
of pharmacological activities like antimicrobial, antiparasitic, anti-inflammatory, anticancer
[5-13]
etc.
MATERIALS AND METHODS
Melting point were recorded in open capillaries and on Veergo melting point apparatus. The
1
H NMR Spectra were recorded on a Bruker 300 MHz using TMS as an internal standard.
The IR spectra were recorded on a Perkin Elmer Spectrum 100 FTIR Spectrophotometer and
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World Journal of Pharmaceutical Research
the Mass Spectra on a Waters Micromass Q-fit instrument. The chemical used are of A.R.
grade.
Procedure for the synthesis of compound
Preparation of dibenzalacetone(1,5-diphenylpenta-1-4-dien-3-one)
In 250ml Erlenmeyer flask dissolve 7.5 gm. of sodium hydroxide in 75 ml DI water and 60
ml of ethanol. Maintain the temperature of the solution at 20-25 º C. Add previously prepared
mixture of 7.5 ml of Benzaldehyde and 3 ml Acetone shake well . A precipitate forms in 2-3
min. after 15 min add the remaining portion of the Benzaldehyde –Acetone mixture , shake
for further 30 min now cool the Erelnmeyer flask and separate
the solid precipitated was
filtered, washed and recrystalized from hot Ethanol.
Preparation of (1E,4E)-N,1,5-triphenylpenta-1,4-dien-3-imine
A mixture of dibenzalacetone(2.34 g., 0.01mol.) and aromatic Amine, Aniline (0.913g., 0.01
mol.) was taken in absolute ethanol(20 ml.) and 1-2 drops of glacial acetic acid were added.
Then the mixture was refluxed for 6-8 hours on water bath. The progress of the reaction was
monitored by TLC. The excess solvent was distilled off and then remaining residue was
poured in crushed ice. The separated solid was filtered, washed and recrystalized from
ethanol. Their physical constant data given in Table 1.
Preparation of (1E,4E)-N-(3-nitrophenyl)-1,5-diphenylpenta-1,4-dien-3-imine
A mixture of dibenzalacetone(2.34 g., 0.01mol.)and aromatic Amine, 3-nitro Aniline (1.38g.,
0.01 mol.) was taken in absolute ethanol(20 ml.) and 1-2 drops of glacial acetic acid were
added. Then the mixture was refluxed for 6-8 hours on water bath. The progress of the
reaction was monitored by TLC. The excess solvent was distilled off and then remaining
residue was poured in crushed ice. The separated solid was filtered, washed and recrystalized
from ethanol. Their physical constant data given in Table 1.
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Preparation of (1E,4E)-N-(4-nitrophenyl)-1,5-diphenylpenta-1,4-dien-3-imine
A mixture of dibenzalacetone(2.34 g., 0.01mol.)and aromatic Amine, 4-nitro Aniline (1.38g.,
0.01 mol.) was taken in absolute ethanol(20 ml.) and 1-2 drops of glacial acetic acid were
added. Then the mixture was refluxed for 6-8 hours on water bath. The progress of the
reaction was monitored by TLC. The excess solvent was distilled off and then remaining
residue was poured in crushed ice. The separated solid was filtered, washed and recrystalized
from ethanol. Their physical constant data given in Table 1
Preparation of 4-{[(1E,4E)-1,5-diphenylpenta-1,4-dien-3-ylidene]amino}
benzenesulfonic acid
A
mixture
of
dibenzalacetone(2.34
g.,
0.01mol.)and
aromatic
Amine,
4-
aminobenzenesulfonic acid (1.73g., 0.01 mol.) was taken in absolute ethanol(20 ml.) and 1-2
drops of glacial acetic acid were added. Then the mixture was refluxed for 6-8 hours on water
bath. The progress of the reaction was monitored by TLC. The excess solvent was distilled
off and then remaining residue was poured in crushed ice. The separated solid was filtered,
washed and recrystalized from ethanol. Their physical constant data given in Table 1
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Preparation of (1E,4E)-N-(4-methylphenyl)-1,5-diphenylpenta 1,4-dien-3-imine
A mixture of dibenzalacetone(2.34 g., 0.01mol.)and aromatic Amine, 4-methylaniline
(1.07g., 0.01 mol.) was taken in absolute ethanol(20 ml.) and 1-2 drops of glacial acetic acid
were added. Then the mixture was refluxed for 6-8 hours on water bath. The progress of the
reaction was monitored by TLC. The excess solvent was distilled off and then remaining
residue was poured in crushed ice. The separated solid was filtered, washed and recrystalized
from ethanol. Their physical constant data given in Table 1.
RESULT AND DISCUSSION
Table. 1
Comp.
Name
Kpp-1
Kpp-2
Kpp-3
Kpp-4
Kpp-5
Molecular
formula
C23H19N
C23H18N2O2
C23H18N2O2
C23H18NO3S
C24H21N
Molcular
weight
309.40
354.40
354.40
389.46
323.43
M.P
°C
150
141
88
99
101
Yield
%
35
28.8
82
53.5
42
% of
C
89.28
77.95
77.95
70.93
89.12
% of
H
6.19
5.12
5.12
4.92
6.54
% of
N
4.53
7.90
7.90
3.60
4.33
Various Schiff’s base derivatives kpp-1-5 were prepared using of dibenzalacetone (1,5diphenylpenta-1-4-dien-3-one)with aromatic amine in presence 1ml. of glacial acetic acid
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gave Schiff base derivatives series kpp1-5. All the compounds synthesized were adequately
characterized by their elemental analyses and spectral IR, 1H-NMR and Mass Spectra.
Spectra study of (1E,4E)-N,1,5-triphenylpenta-1,4-dien-3-imine
IR(KBr. cm-1):1622 cm-1(C=N), 1235 cm-1(N=CH str), 1036 cm-1, 1010(CH=N),3420 cm1
(N-H),1438
cm-1
(C=N,
Ar),
1H
NMR(ppm)
(CDCl3):5.56(s,1H,Ar-H),6.66-
6.68(m,4H,Ar-H),2.59(s,3H,CH3), MS:310.40[M+1].
Spectra study of (1E,4E)-N-(3-nitrophenyl)-1,5-diphenylpenta 1,4-dien-3-imine
IR(KBr. cm-1):1637 cm-1(C=N), 1235 cm-1(N=CH str),1023(CH=N),3520 cm-1(NH),1330,1550(-No2Ar),898,760(M-Sub)1HNMR(ppm)
(CDCl3):5.26(s,1H,Ar-H),6.59-6.62(m,4H,Ar-H)5.79(s,N-H) MS:355.40[M+1].
Spectra study of (1E,4E)-N-(4-nitrophenyl)-1,5-diphenylpenta-1,4-dien-3-imine
IR(KBr. cm-1):1645 cm-1(C=N), 1256 cm-1(N=CH str),1017(CH=N),3560 cm-1(NH),1359,1550(-No2 Ar), 770,850(P-Sub)1HNMR(ppm)
(CDCl3):7.2(s,1H,Ar-H),6-7(m,4H,Ar-H)5.06(s,N-H) MS:355.40[M+1].
Spectra study of (1E,4E)-N-(4-methylphenyl)-1,5-diphenylpenta
1,4-dien-3-imine
IR(KBr. cm-1):1636 cm-1(C=N), 1200cm-1(N=CH str),1015(CH=N),3480
cm-1(N-H),1HNMR(ppm) (CDCl3):5.46(s,1H,Ar-H),6.62-6.64
(m,4H,Ar-H)5.89(s,N-H) MS:324.43[M+1].
Spectra
study
of
4-{[(1E,4E)-1,5-diphenylpenta-1,4-dien-3-
ylidene]amino}
benzenesulfonic acid
IR(KBr. cm-1):1644 cm-1(C=N), 1234cm-1(N=CH str),1046(CH=N),3451
cm-1(N-H),1HNMR(ppm)
(CDCl3):5.46(s,1H,Ar-H),6-7(m,4H,Ar-H)
5.89(s,N-H)
MS:390.46[M+1].
ACKNOWLEDGEMENTS
We are thankful to The H. N. S. B. Ltd. Science College, Himatnagar for providing excellent
facilities and we are grateful to my guide Dr. S.P.Vyas Sir and Dr. Z. M. Gadhawala sir (P.G.
In-charge, Organic Chemistry).
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REFERENCES
1. Selvam, P.; Chandramohan, M.; De Clercq, E.; Witvrouw, M.; Pannecouque, C. Eur J
Pharm Sci., 2001; 14(4): 313.
2. More, P. G.; Bhalvankar, R. B.; Pattar, S. C.; J Indian Chem Soc., 2001; 78: 474-475.
3. Bayer, E. Chem Ber., 1957; 90(10): 2325.
4. Amanda,J Gallant; Brian O Patrick; Mark J MacLachlan; J Org Chem., 2004; 69(25):
8739.
5. Chambhare, R. V.; Khadse, B. G.; Bobde, A. S.; Bahekar, R. H. Eur J Med Chem., 2003;
38(7): 89.
6. Rathelot, P.; Azas, N.; El-Kashef, H.; Delmas, F. Eur J Med Chem., 2002; 37(8): 671.
7. Holla, B. S.; Malini, K. V.; Rao, B. S.; Sarojini, B. K.; Kumari, N. S. Eur J Med Chem.,
2003; 38(7): 313.
8. Holla, B. S.; Veerendra, B.; Shivananda, M. K.; Poojary, B. Eur J Med Chem., 2003;
38(7): 759.
9. Parikh, K. S.; Vyas, S. P. American J of Pharmtech Research, 2012; 2(1): 570.
10. Parikh, K. S.; Vyas, S. P. Der Chemica Sinica, 2012; 3(2): 426.
11. Parikh, K. S.; Vyas, S. P. Der Chemica Sinica, 2012; 3(2): 430.
12. Parikh, K. S.; Vyas, S. P. Int. Journal of Phrm. Sci. and Res., 2012; 3(9): 3425-3427.
13. Parikh, K. S.; Vyas, S. P. Asian J. of Biochemical and Phar. Res., 2012; 3(2): 1-7.
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